NP-MRD: Showing NP-Card for 3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate (NP0306737)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 23:24:50 UTC

Updated at

2022-09-10 23:24:50 UTC

NP-MRD ID

NP0306737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate

Description

(3B,24R,25x)-26-Benzoyloxystigmast-5-ene-3-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3b,24R,25x)-26-Benzoyloxystigmast-5-ene-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (3b,24R,25X)-26-benzoyloxystigmast-5-ene-3-ol has been detected, but not quantified in, brassicas. 3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate is found in Lepidium sativum. This could make (3b,24R,25X)-26-benzoyloxystigmast-5-ene-3-ol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307542D          

 39 43  0  0  0  0            999 V2000
   12.7962   -3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0157   -3.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1597   -1.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3630   -5.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6056   -4.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9875   -3.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3757    1.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9212    0.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5670    1.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6580   -0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3038    0.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3699   -3.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6332   -3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0555   -7.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7743   -7.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757   -5.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838   -6.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254   -6.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818   -5.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6441   -5.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8006   -4.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6266   -7.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5140   -1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5612   -4.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7052   -2.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4420   -2.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8492   -0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -7.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9166   -7.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7831   -6.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2980   -4.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5019   -5.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0730   -5.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5860   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3543   -6.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5106   -5.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978   -7.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1314   -1.6731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7773   -1.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 24  2  1  0  0  0  0
 24 12  1  0  0  0  0
 25  3  1  0  0  0  0
 25 23  1  0  0  0  0
 26  6  1  0  0  0  0
 26 13  1  0  0  0  0
 26 25  1  0  0  0  0
 27 10  2  0  0  0  0
 27 11  1  0  0  0  0
 28 14  2  0  0  0  0
 28 22  1  0  0  0  0
 29 18  1  0  0  0  0
 29 22  1  0  0  0  0
 30 15  1  0  0  0  0
 31 16  1  0  0  0  0
 31 24  1  0  0  0  0
 32 17  1  0  0  0  0
 32 30  1  0  0  0  0
 33 19  1  0  0  0  0
 33 30  1  0  0  0  0
 34 27  1  0  0  0  0
 35  4  1  0  0  0  0
 35 20  1  0  0  0  0
 35 28  1  0  0  0  0
 35 33  1  0  0  0  0
 36  5  1  0  0  0  0
 36 21  1  0  0  0  0
 36 31  1  0  0  0  0
 36 32  1  0  0  0  0
 37 29  1  0  0  0  0
 38 34  2  0  0  0  0
 39 23  1  0  0  0  0
 39 34  1  0  0  0  0
M  END

     RDKit          3D

 93 97  0  0  0  0  0  0  0  0999 V2000
    2.0361   -1.7020   -2.8372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -1.3805   -1.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4243    0.0697   -1.8072 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4629    1.0631   -1.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7194    1.2504   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6887    0.3354    0.3361 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1738   -0.9969    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530    0.4450   -0.4683 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1002    1.8404   -0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973    1.7152   -0.9319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8117    0.2427   -0.9507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1891   -0.0717   -0.5333 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7176   -1.3863   -0.9806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1859   -1.3548   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6409   -0.7871    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1111   -0.7637    0.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5413    0.6851    0.3919 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7363    0.9123    1.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4466    1.6438    0.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5361    1.0727    1.8496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7964   -0.1644    1.3642 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7982   -1.1136    2.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    0.1707    0.9387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3544   -0.5049    1.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082   -0.6991    1.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071   -0.4339   -0.1702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4428   -1.7473   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8294    0.2519   -1.2390 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2095    1.6973   -1.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0512   -0.4668    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3609   -0.2681    0.5364 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4818   -0.6699   -0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3820   -1.2534   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7933   -0.4261    0.4160 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9211    0.2136    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1637    0.4689    2.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2830    0.0678    1.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1995   -0.5763    0.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9322   -0.8194   -0.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3345   -0.8608   -2.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5096   -2.6357   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4064   -1.8864   -3.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0981   -1.7872   -2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1547   -1.9429   -0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379    0.3353   -2.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    1.0316   -2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9392    2.0807   -1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2581    2.2945   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4834    1.3335    0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4035    0.8190    1.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0101   -1.8117   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -1.0152    0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6871   -1.3829    1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2830    0.2741   -1.5530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281    2.3060    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    2.4827   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420    2.1899   -1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997    2.2948   -0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7368   -0.0477   -2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8462    0.7054   -1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533   -2.2453   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5745   -1.4848   -2.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8623   -1.8190   -1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6038   -1.4557   -0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3181   -1.0888    1.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6875    0.8098   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6439    1.7330    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8571    2.0127   -0.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9351    2.5327    1.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1377    0.8907    2.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7744    1.8473    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1272   -0.7991    3.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8340   -1.0576    3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7064   -2.1586    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2801    1.2642    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904   -1.5257    2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3356   -0.0182    2.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6504   -1.7548    1.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042   -0.0795    1.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2432   -2.5811   -0.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -2.0423   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6373   -1.5917   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5117   -0.2011   -1.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8153    2.1822   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9566    2.2627   -2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244    1.7360   -1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916   -0.0460    0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9240   -1.5657   -0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0644    0.5519    2.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2903    0.9684    3.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2853    0.2520    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1072   -0.8743   -0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8806   -1.3227   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  3 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 26  8  1  0
 39 34  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  3 45  1  6
  4 46  1  0
  4 47  1  0
  5 48  1  0
  5 49  1  0
  6 50  1  1
  7 51  1  0
  7 52  1  0
  7 53  1  0
  8 54  1  6
  9 55  1  0
  9 56  1  0
 10 57  1  0
 10 58  1  0
 11 59  1  6
 12 60  1  6
 13 61  1  0
 13 62  1  0
 14 63  1  0
 16 64  1  0
 16 65  1  0
 17 66  1  6
 18 67  1  0
 19 68  1  0
 19 69  1  0
 20 70  1  0
 20 71  1  0
 22 72  1  0
 22 73  1  0
 22 74  1  0
 23 75  1  6
 24 76  1  0
 24 77  1  0
 25 78  1  0
 25 79  1  0
 27 80  1  0
 27 81  1  0
 27 82  1  0
 28 83  1  6
 29 84  1  0
 29 85  1  0
 29 86  1  0
 30 87  1  0
 30 88  1  0
 35 89  1  0
 36 90  1  0
 37 91  1  0
 38 92  1  0
 39 93  1  0
M  END


  Mrv0541 05061307542D          

 39 43  0  0  0  0            999 V2000
   12.7962   -3.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0157   -3.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1597   -1.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3630   -5.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6056   -4.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9875   -3.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3757    1.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9212    0.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5670    1.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6580   -0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3038    0.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3699   -3.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6332   -3.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0555   -7.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7743   -7.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7757   -5.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838   -6.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254   -6.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818   -5.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6441   -5.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8006   -4.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6266   -7.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5140   -1.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5612   -4.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7052   -2.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4420   -2.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8492   -0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3454   -7.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9166   -7.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7831   -6.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2980   -4.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5019   -5.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0730   -5.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5860   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3543   -6.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5106   -5.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978   -7.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1314   -1.6731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7773   -1.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 13 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 24  2  1  0  0  0  0
 24 12  1  0  0  0  0
 25  3  1  0  0  0  0
 25 23  1  0  0  0  0
 26  6  1  0  0  0  0
 26 13  1  0  0  0  0
 26 25  1  0  0  0  0
 27 10  2  0  0  0  0
 27 11  1  0  0  0  0
 28 14  2  0  0  0  0
 28 22  1  0  0  0  0
 29 18  1  0  0  0  0
 29 22  1  0  0  0  0
 30 15  1  0  0  0  0
 31 16  1  0  0  0  0
 31 24  1  0  0  0  0
 32 17  1  0  0  0  0
 32 30  1  0  0  0  0
 33 19  1  0  0  0  0
 33 30  1  0  0  0  0
 34 27  1  0  0  0  0
 35  4  1  0  0  0  0
 35 20  1  0  0  0  0
 35 28  1  0  0  0  0
 35 33  1  0  0  0  0
 36  5  1  0  0  0  0
 36 21  1  0  0  0  0
 36 31  1  0  0  0  0
 36 32  1  0  0  0  0
 37 29  1  0  0  0  0
 38 34  2  0  0  0  0
 39 23  1  0  0  0  0
 39 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)COC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C36H54O3/c1-6-26(25(3)23-39-34(38)27-10-8-7-9-11-27)13-12-24(2)31-16-17-32-30-15-14-28-22-29(37)18-20-35(28,4)33(30)19-21-36(31,32)5/h7-11,14,24-26,29-33,37H,6,12-13,15-23H2,1-5H3

> <INCHI_KEY>
BJZQJLWLEFGCBH-UHFFFAOYSA-N

> <FORMULA>
C36H54O3

> <MOLECULAR_WEIGHT>
534.8122

> <EXACT_MASS>
534.407295594

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
66.12796253329248

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-ethyl-6-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-2-methylheptyl benzoate

> <ALOGPS_LOGP>
7.50

> <JCHEM_LOGP>
8.981051754

> <ALOGPS_LOGS>
-7.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20428950550382

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972423776486518

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
161.43980000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethyl-6-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-2-methylheptyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      23.886  -6.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.829  -6.408   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.831  -2.880   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.878 -10.210   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.064  -7.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.377  -6.650   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.835   2.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.853   1.255   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.325   2.107   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.362  -0.204   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.834   0.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.357  -7.259   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.849  -5.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.170 -14.074   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.512 -13.318   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.248 -10.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.330 -11.514   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.194 -11.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.219  -9.454   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.536 -10.966   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.561  -8.698   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.503 -14.046   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.359  -3.731   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.848  -7.563   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.850  -4.036   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.358  -5.495   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.852  -0.508   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.845 -13.290   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.178 -13.262   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.528 -11.778   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.356  -9.022   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.870 -11.022   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.203 -10.994   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.361  -1.968   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.861 -11.750   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.886  -9.482   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.836 -14.017   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      26.379  -3.123   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      23.851  -2.272   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   35                                                            
CONECT    5   36                                                            
CONECT    6    1   26                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   27                                                       
CONECT   11    9   27                                                       
CONECT   12   13   24                                                       
CONECT   13   12   26                                                       
CONECT   14   15   28                                                       
CONECT   15   14   30                                                       
CONECT   16   17   31                                                       
CONECT   17   16   32                                                       
CONECT   18   20   29                                                       
CONECT   19   21   33                                                       
CONECT   20   18   35                                                       
CONECT   21   19   36                                                       
CONECT   22   28   29                                                       
CONECT   23   25   39                                                       
CONECT   24    2   12   31                                                  
CONECT   25    3   23   26                                                  
CONECT   26    6   13   25                                                  
CONECT   27   10   11   34                                                  
CONECT   28   14   22   35                                                  
CONECT   29   18   22   37                                                  
CONECT   30   15   32   33                                                  
CONECT   31   16   24   36                                                  
CONECT   32   17   30   36                                                  
CONECT   33   19   30   35                                                  
CONECT   34   27   38   39                                                  
CONECT   35    4   20   28   33                                             
CONECT   36    5   21   31   32                                             
CONECT   37   29                                                            
CONECT   38   34                                                            
CONECT   39   23   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
3-Ethyl-6-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-2-methylheptyl benzoic acid	Generator

Chemical Formula

C₃₆H₅₄O₃

Average Mass

534.8122 Da

Monoisotopic Mass

534.40730 Da

IUPAC Name

3-ethyl-6-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-2-methylheptyl benzoate

Traditional Name

3-ethyl-6-{5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-2-methylheptyl benzoate

CAS Registry Number

Not Available

SMILES

CCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)COC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C36H54O3/c1-6-26(25(3)23-39-34(38)27-10-8-7-9-11-27)13-12-24(2)31-16-17-32-30-15-14-28-22-29(37)18-20-35(28,4)33(30)19-21-36(31,32)5/h7-11,14,24-26,29-33,37H,6,12-13,15-23H2,1-5H3

InChI Key

BJZQJLWLEFGCBH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lepidium sativum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.5	ALOGPS
logP	8.98	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	161.44 m³·mol⁻¹	ChemAxon
Polarizability	66.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0034553

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013060

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85192466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate (NP0306737)

MOL for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

3D MOL for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

3D SDF for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

3D-SDF for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

PDB for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

3D PDB for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

SMILES for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

INCHI for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

Structure for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)

3D Structure for NP0306737 (3-ethyl-6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptyl benzoate)